Find Hotels with a Pool in Wainscott, NY

Check prices for these dates

Tonight
Nov 10 - Nov 11
Tomorrow
Nov 11 - Nov 12
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Wainscott hotels with a pool

A swimming pool with two lounge chairs and a green umbrella.

1. The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (297 reviews)
  • cleanliness
    Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun.
$241 nightly
The price is $275
Nov 15 - Nov 16
Total with taxes and fees
The Sagaponack
A swimming pool with a wooden fence, a grassy yard, and a white building in the background.

2. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
Wainscott
10.0 out of 10, Exceptional, (34 reviews)
$1,782 nightly
The price is $2,035
Nov 18 - Nov 19
Total with taxes and fees
Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
Outdoor pool

3. East Hampton House Resort

East Hampton House Resort
3.0 star property
East Hampton North
9.0 out of 10, Wonderful, (353 reviews)
  • cleanliness
    Seasonal outdoor pool creates a refreshing escape at this hotel, with tennis courts and gardens adding to the resort atmosphere.
$173 nightly
The price is $197
Nov 24 - Nov 25
Total with taxes and fees
East Hampton House Resort
A pool area with lounge chairs and an umbrella, surrounded by lush greenery.

4. Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (211 reviews)
  • cleanliness
    Seasonal poolside splendor at East Hampton hotel with complimentary bikes and garden views.
$170 nightly
The price is $194
Nov 23 - Nov 24
Total with taxes and fees
Journey East Hampton
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.

5. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (687 reviews)
  • cleanliness
    Swim into serenity at this charming Sag Harbor retreat with a seasonal outdoor pool and balcony views.
$219 nightly
The price is $250
Nov 11 - Nov 12
Total with taxes and fees
Sag Harbor Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a forested area.

6. A Room At The Beach

A Room At The Beach
3.0 star property
Bridgehampton
9.2 out of 10, Wonderful, (106 reviews)
  • cleanliness
    Soak up sunshine and serene vibes at this Hamptons motel with a stylish outdoor pool.
$296 nightly
The price is $338
Nov 12 - Nov 13
Total with taxes and fees
A Room At The Beach
A pool area with umbrellas, potted plants, and a pathway leading to a building.

7. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (321 reviews)
  • cleanliness
    Dive into summer splendor at a tranquil pool retreat with chic cabanas and luxe loungers.
$356 nightly
The price is $407
Dec 6 - Dec 7
Total with taxes and fees
Faraway Sag Harbor
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.

8. Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (165 reviews)
  • cleanliness
    Serene outdoor pool creates luxurious oasis in the Hamptons; perfect for unwinding after coastal adventures.
$621 nightly
The price is $713
Nov 15 - Nov 16
Total with taxes and fees
Topping Rose House
A house with a sloped roof, large windows, and a pathway leading to the entrance.

9. Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (90 reviews)
  • cleanliness
    Soak in serene poolside moments at this charming Colonial B&B with a garden terrace for ultimate relaxation.
$411 nightly
The price is $470
Nov 11 - Nov 12
Total with taxes and fees
Mill House Inn
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.

10. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (615 reviews)
  • cleanliness
    Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
$139 nightly
The price is $159
Nov 17 - Nov 18
Total with taxes and fees
The Bentley Hotel Southampton
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Wainscott

Breakfast included
4 stars

Top Wainscott Hotel Reviews

A swimming pool with two lounge chairs and a green umbrella.
The Sagaponack

The Sagaponack

The Sagaponack
Wainscott

10/10 Excellent

We loved the 1 bedroom bungalow! One could sleep while the other read or watched TV. The bed was very comfortable. The kitchenette was very convenient. While there was a little road noise, the thoughtfully provided sound machine canceled that out. The best part for us was the location; right in the middle of the Hamptons, Montauck and Sag Harbor. Would definitely stay here again!
United States
PAUL
Reviewed November 9, 2026
The Sagaponack

Frequently Asked Questions

How much does a hotel with outdoor pool in Wainscott cost?

Enjoy staying in a hotel in Wainscott with an outdoor pool. You can find a great deal from $159 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.

Are there hotels in Wainscott with outdoor pool cabanas or loungers?

The Sagaponack is a charming 3-star hotel in Wainscott that offers a delightful outdoor pool experience. Guests rave about the inviting pool area, featuring comfortable sun loungers and shaded umbrellas, great for lounging on a sunny day. With a review rating of 8.8, visitors appreciate the hotel's friendly staff and the nice decor that adds to the overall appeal.

Beyond the pool, The Sagaponack also provides complimentary toiletries and free WiFi, ensuring a convenient stay for families. Plus, self-parking is available at no additional cost, making it easy to explore the beautiful surroundings of Wainscott.

Is it cheaper to book flights and a Wainscott hotel with a pool as a package?

Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it’s wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.

Can I cancel my hotel reservation on Expedia?

Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Wainscott for you.

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